Nitric Acid → 4-Isobutyl-3-nitrobenzaldehyde

HRID 1777333Notes

Reaction equation

HRID 1777333 reaction equation
[CH2:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].S(=O)(=O)(O)O.[N+:18]([O-])([OH:20])=[O:19]>>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:9]=[O:10])=[CH:11][C:12]=1[N+:18]([O-:20])=[O:19])[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 577537Benzaldehyde, 4-(2-methylpropyl)-

Product 1

HCID 867151394-Isobutyl-3-nitrobenzaldehyde

Procedure

4-Isobutyl benzaldehyde (7 g, 0.0431 mol) is added drop wise to a mixture of concentrated sulfuric acid & nitric acid (68-72%) (9:1, 60 mL) at 0-5° C. Reaction mixture is allowed to stir at this temperature for 2 hrs, then poured into crushed ice. It is then extracted with ethyl acetate (3×40 mL). Combined organic layer is dried over sodium sulfate and concentrated under reduced pressure. The residue is purified by column chromatography (silica gel, 230-400 mesh, ethyl acetate:n-hexane 1:19) to yield 4-isobutyl-3-nitrobenzaldehyde.

Workup

  1. customReaction mixture
  2. additionpoured
  3. custominto crushed ice
  4. extractionIt is then extracted with ethyl acetate (3×40 mL)
  5. dry with materialCombined organic layer is dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by column chromatography (silica gel, 230-400 mesh, ethyl acetate:n-hexane 1:19)

Sources & evidence

ORD record
ord-bd94ea56358241e7ac94cfed83649f21
Source dataset
uspto-grants-2016_02
Patent number
US09266867B2

Reaction notes

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